| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1343633 | Tetrahedron: Asymmetry | 2015 | 8 Pages |
A series of racemic trans-1,2,3,4-tetrahydronaphthalen-2-ols bearing an azole nucleus at the C-1 or C-3 position has been synthesized by ring opening reactions of the corresponding epoxides using imidazole or 1,2,4-triazole. The kinetic resolutions of these racemates were undertaken through transesterification processes, finding good levels of activities and high to excellent enantiodiscrimination values for the Pseudomonas cepacia lipase immobilized on a ceramic carrier. Investigations into the optimum reaction conditions were carried out by consideration of different organic solvents, temperatures, enzyme loadings, and reaction times. With the best conditions in hand, the experiments were later carried out toward the resolution of the related racemic cis-alcohols, which were previously obtained through a Mitsunobu and deprotection chemical sequence from the trans-stereoisomers.
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(2R,3R)-3-(1H-Imidazol-1-yl)-1,2,3,4-tetrahydronaphthalen-2-yl acetateC15H16N2O2Ee = 99% (HPLC, Chiralcel OD-H)[α]D20 = −4.5 (c 1.0, MeOH)Source of chirality: Lipase-catalyzed resolution with PSLAbsolute configuration: (2R,3R)
(2S,3S)-3-(1H-Imidazol-1-yl)-1,2,3,4-tetrahydronaphthalen-2-olC13H14N2OEe = 83% (HPLC, Column Chiralcel OD-H)[α]D20 = +26.0 (c 1.0, MeOH)Source of chirality: Lipase-catalyzed resolution with PSLAbsolute configuration: (2S,3S)
(2R,3S)-3-(1H-Imidazol-1-yl)-1,2,3,4-tetrahydronaphthalen-2-yl acetateC15H16N2O2Ee = 99% (HPLC, Column Chiralcel OJ-H)[α]D20 = −14.4 (c 0.5, MeOH)Source of chirality: Lipase-catalyzed resolution with PSLAbsolute configuration: (2R,3S)
(2S,3R)-3-(1H-Imidazol-1-yl)-1,2,3,4-tetrahydronaphthalen-2-olC13H14N2OEe = 94% (HPLC, Column Chiralpak IC)[α]D20 = +39.0 (c 1.0, MeOH)Source of chirality: Lipase-catalyzed resolution with PSLAbsolute configuration: (2S,3R)
(2R,3R)-3-(1H-1,2,4-Triazol-1-yl)-1,2,3,4-tetrahydronaphthalen-2-yl acetateC14H15N3O2Ee = >99% (HPLC, Column Chiralcel OD-H)[α]D20 = −28.6 (c 1.0, MeOH)Source of chirality: Lipase-catalyzed resolution with PSLAbsolute configuration: (2R,3R)
(2S,3S)-3-(1H-1,2,4-Triazol-1-yl)-1,2,3,4-tetrahydronaphthalen-2-olC12H13N3OEe = 93% (HPLC, Column Chiralcel OD-H)[α]D20 = +35.0 (c 1.0, MeOH)Source of chirality: Lipase-catalyzed resolution with PSLAbsolute configuration: (2S,3S)
(2R,3S)-3-(1H-1,2,4-Triazol-1-yl)-1,2,3,4-tetrahydronaphthalen-2-yl acetateC14H15N3O2Ee = >99% (HPLC, Column Chiralcel OD-H)[α]D20 = −29.0 (c 1.0, MeOH)Source of chirality: Lipase-catalyzed resolution with PSLAbsolute configuration: (2R,3S)
(2S,3R)-3-(1H-1,2,4-Triazol-1-yl)-1,2,3,4-tetrahydronaphthalen-2-olC12H13N3OEe = 29% (HPLC, Column Chiralcel OD-H)[α]D20 = +4.0 (c 1.0, MeOH)Source of chirality: Lipase-catalyzed resolution with PSLAbsolute configuration: (2S,3R)
(1R,2R)-1-(1H-Imidazol-1-yl)-1,2,3,4-tetrahydronaphthalen-2-yl acetateC15H16N2O2Ee = >99% (HPLC, Column Chiralpak IC)[α]D20 = +7.0 (c 1.0, MeOH)Source of chirality: Lipase-catalyzed resolution with PSLAbsolute configuration: (1R,2R)
(1S,2S)-1-(1H-Imidazol-1-yl)-1,2,3,4-tetrahydronaphthalen-2-olC13H14N2OEe = 85% (HPLC, Column Chiralpak IC)[α]D20 = −2.1 (c 1.0, MeOH)Source of chirality: Lipase-catalyzed resolution with PSLAbsolute configuration: (1S,2S)
(1S,2R)-1-(1H-Imidazol-1-yl)-1,2,3,4-tetrahydronaphthalen-2-yl acetateC15H16N2O2Ee = 98% (HPLC, Column Chiralpak IC)[α]D20 = +16.7 (c 1.0, MeOH)Source of chirality: Lipase-catalyzed resolution with PSLAbsolute configuration: (1S,2R)
(1R,2S)-1-(1H-Imidazol-1-yl)-1,2,3,4-tetrahydronaphthalen-2-olC13H14N2OEe = 98% (HPLC, Column Chiralpak IC)[α]D20 = −3.2 (c 1.0, MeOH)Source of chirality: Lipase-catalyzed resolution with PSLAbsolute configuration: (1R,2S)
